I set my If/Then to identify if a field was upper or lower case in formula expression #1. Then in formula expression #2, I turned all the Scores to lowercase so they would Summarize properly in my next tool. What I found was that formula expression #1 re-evaluated based on the results of #2, even though #2 came after #1

I got around it by just creating a brand new column called Player, but I wasn't expecting that to happen, since that's not how Desktop behaves

FYI
@AYXAcademy - Not sure if this is a bug or how Designer Cloud is expected to behave. Let me know if I should make a Support ticket